Tall Ship Windy: Chicago Skyline Sails & Historic Tall Ship Cruises
Difficulty
easy
Duration
1.5–3 hours
Fitness Level
Accessible for most fitness levels; ability to stand and move on deck recommended
Overview
Step aboard Chicago's official tall ship and experience the city skyline like never before. From educational sails to fireworks cruises, Tall Ship Windy offers unique lake adventures on Lake Michigan.
Tall Ship Windy: Chicago Skyline Sails & Historic Tall Ship Cruises
Adventure Tips
Arrive Early for Boarding
Plan to arrive 15-30 minutes before your scheduled sail to get settled and meet the crew.
Dress in Layers
Lake Michigan’s breeze can be chilly even in summer evenings; bring a windbreaker or layers.
Bring a Camera with a Zoom Lens
Capture close-ups of the sails, crew working, and city skyline from varying perspectives.
Participate in Raising the Sails
Feel free to engage with the crew and try your hand at hoisting sails for a hands-on experience.
Local Insights
Wildlife
- Migrating ring-billed gulls common over Lake Michigan
- Occasional sightings of lake trout near the shore
History
Tall Ship Windy recalls Chicago’s nautical past, featuring traditional sailing methods on Lake Michigan, once key to the city’s trade and transport.
Conservation
The ship promotes awareness of lake ecosystem health and practices sustainable sailing to minimize environmental impact on Lake Michigan.
Adventure Hotspots in Chicago
No adventures found in this area.
Frequently Asked Questions
Recommended Gear
Windbreaker or Light Jacket
Protects against lake breeze and changing weather, especially in cooler evenings.
spring|summer|fall specific
Non-slip Footwear
Ensures steady footing on occasionally wet or moving decks.
Sunscreen
Crucial for daytime sails to guard against sun exposure on open water.
summer specific
Camera or Smartphone
Capture memorable views of Chicago’s skyline and aboard the historic vessel.